New nitroarylaminoanthraquinone compound



Patented Sept. 1, 1931 HEINEIOHTLTESOHEQANE ALEEIWr JOE,-`OE ELBEEEEm),l COLOGNE, GEEMANY, Assieiyronsy Tof GENERAL ANILINE WORKS, ING., OE. NEW YORK; N. Y., A coEEoEA-i 1 f NEW, N1:uEoEnAlvLI-NOAN'LHEEL,QUINONEA OONEOUNE med Octobf 12, 19'25, we have described newV N-ntrosoarylamino anthraquinones of the,`

the l"e'iyflf radicle. iThe yield Ofths reaction i group" is 'aftche'd t6 f #bei isolated.bxlteringpi. It is .alsepessible .te

`im thisease, beingconverted into the nitrO cqmpo'lyiliids I iE the ynesnen'tV state.

This noyel reacti' proceeds as Well with alpha as with hetze, with mOO-, di, or polye quille@ nuclus can be further substitufedii e dissolye in ys'lilfugi v acid, sulfurie-beric acid.

They are, denlyelvred., CryStalline Sub-V ffjeili violet to blue,` gijeen, Olive andbiowii.

@eine cu), NIE-.0131

sodium nitrite added and the miXture heated to` the boiling point. The color of the solution turns dark and the orange colored nitrol-p-toluidoanthraquinone separates into a practically quantitative-yield. The'product is identical Withthat obtained in Example l.

Sodium nitrite can be replaced in this reaction'by amyl nitritefetc.V

(3) lpart 1-p-toluidoanthraquinone is dis- 1o solved in 10-20 parts boiling glacial acetic acid and slowly at that temperature sodium. nitrite added. The'reaction'is complete in a few minutes andthe orange colorednitro-lp-toluidoanthraquinone, identical `"with the i V product of Example l, separates out.

part 4v,l#Lidi-p-toluidoanthraoluinoiie is dissolved in130 parts boiling glacial acetic f acid and sodium nitrite added until the crysv.tallization ofthe bluish-black needles of the;

'i dinitro-l-tdip-toluidoanthraquinoneis complete. vrThe productl is filtered olf and isolated inthe usualmanner.

The lappearanceand color reactions of some of our novel nitro-arylaminoanthraquinones 4. In processes oie producingV nitro-l-ptoluidoanthraquinone the step comprising heating N-nitroso-lp-toluidoanthraquinone at temperaturesabove 70 C. in the presence of an organic acidand of a nitrite compound.

5. In processes of produ'cingnitro-l-ptoluidoanthraquinone the step comprising heating to boiling temperature N-nitroso-l-pf toluidoanthraquinonein glacial acetic acid.

6. In processes otproducing nitrofl-ptoluidoanthraquinone the step comprising heating to boiling temperature N-nitroso-l-ptoluidoanthraquinone in glacial acetic acid Vin the presence of an alkali' metal nitrite. e

7. In the processof producing nitroaryly' aminoanthraquinone compounds, 1 the steps which' comprise 'reacting withja nitrous acid compound, at a'temperature below about 40 f C., upon, an arylaminoanthraquinone compound dissolved in an organic acid, and then heatingV this solution at atemperature above 700C.

8. In the process of producing nitroary'laminoanthr'aquinone compounds, the steps .We elaine,-`

processes V.producing.l n.itroajrrylv 5'0""aminoarithraquindllev compounds fhe." Stel"V comprising heating N-'nitrosoarylaminoanf thraquinone compounds' Laty temperatures` above0 C.V the presence of anorganic acid. i

comprising heating N-nitrosoarylaminoany thraquinone compounds at `temperatures above 70 C. in the Vpresence of an organic acid and of a nitrous acid compound.

3. In processes of producingrnitro-l-ptoluidoanthraquinone theV step comprising heatingr N-nitroso-lfp-toluidoanthraquinone attemperaturesfabove 70 C. inthe `presence l In' processes ofY producing nitroaryl-- aminoanthraquinone compounds the "step" compound,V4 at atemperature below about' 40 C., upon*v an a-rylaminoanthraquinone'fcomvpound ldissolved in an organic'V acid, and then he'atingifthis solution"atjav temperature above C. yvvhilejadding a further Y(p lantity of a i nitrous acid compoundf '9.1 In the process of producing n i'troifl-pel to-luidoanthraquinone, the steps which compris-e reacting with a nitrous acid compound,

at Y a temperature below about I 40 C., upon l-p-toluidoanthraquinone dissolved in -an organic acid,j`and then heating this'lsolutivon at a temperatureabove 70 C."

to'luidoanthraquinone, the steps which comprisereacting with a nitrous acid compound, at yaV temperature. below about 40 C., upon l-p-toluidoanthraquinone dissolved in an A -12 '10. 'In theprocess'of producingnitro-l-p 

